Question

Examples of strong nucleophiles that can open an epoxide

Answer 1

Strong nucleophiles that can open an epoxide include hydroxide ions (OH¯), alkoxide ions (RO¯), and Grignard reagents (RMgX). These nucleophiles have a high electron density and are capable of attacking the carbon atom in the epoxide ring, opening it up.

Step-by-step explanation:

Strong nucleophiles that can open an epoxide include:

• Hydroxide ion (OH¯)
• Alkoxide ions (RO¯)
• Grignard reagents (RMgX)

These nucleophiles have a high electron density and are capable of attacking the carbon atom in the epoxide ring, opening it up.

Answer 2

Some examples of strong nucleophiles that can open an epoxide are hydroxide ion (OH⁻), alkoxide ions (RO⁻), and amines (NH₃ or RNH₂).

Step-by-step explanation:

Hydroxide ion can attack the less substituted carbon of an epoxide, forming a hydroxy alcohol. Alkoxide ions can attack the more substituted carbon, forming an ether. For example, hydroxide ion (OH⁻) can attack the less substituted carbon of an epoxide, opening the ring and forming a hydroxy alcohol, this reaction is called ring-opening of epoxide.

Another example is the use of alkoxide ions (RO⁻) as nucleophiles. The alkoxide ion can attack the more substituted carbon of the epoxide, leading to the formation of an ether. These nucleophiles are negatively charged (or partially negative) and possess a lone pair of electrons or a negative bond.

When they attack an epoxide, they open the ring by attacking the electrophilic carbon and displacing a leaving group, leading to the formation of a new bond. So therefore hydroxide ion (OH⁻), alkoxide ions (RO⁻), and amines (NH₃ or RNH₂) are examples of strong nucleophiles.